Premium
High specific activity steroids II: Microscale synthesis of norgestrel‐[9,11‐ 3 H]
Author(s) -
Huang Glenn T.,
McCarthy Keith E.,
Parnes Howard
Publication year - 1992
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580311206
Subject(s) - chemistry , tritium , norgestrel , steroid , ketone , ether , microscale chemistry , substrate (aquarium) , specific activity , radiochemistry , tritium illumination , organic chemistry , biochemistry , population , hormone , enzyme , physics , demography , mathematics education , mathematics , oceanography , sociology , family planning , nuclear physics , research methodology , geology
The synthesis of the high specific activity (39 Ci/mmole) tritium labelled steroid norgestrel is described. A practical synthesis of the required substrate for tritium incorporation, 18‐methyl‐Δ 9(11) ‐estradiol‐3‐methyl ether ( 6 ), was developed from norgestrel itself. Following reduction with carrier‐free tritium gas, microscale conditions were employed for the conversion of the resulting labelled intermediate ( 7 ) back to norgestrel‐[9,11‐ 3 H], including a selective in situ protection of the A‐ring ketone of 19‐norandrost‐4‐ene‐3,17‐dione ( 11 ).